CA2983826A1 - Azabenzimidazoles and their use as ampa receptor modulators - Google Patents
Azabenzimidazoles and their use as ampa receptor modulators Download PDFInfo
- Publication number
- CA2983826A1 CA2983826A1 CA2983826A CA2983826A CA2983826A1 CA 2983826 A1 CA2983826 A1 CA 2983826A1 CA 2983826 A CA2983826 A CA 2983826A CA 2983826 A CA2983826 A CA 2983826A CA 2983826 A1 CA2983826 A1 CA 2983826A1
- Authority
- CA
- Canada
- Prior art keywords
- imidazo
- trifluoromethyl
- indazol
- pyridine
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 102000003678 AMPA Receptors Human genes 0.000 title claims description 68
- 108090000078 AMPA Receptors Proteins 0.000 title claims description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 747
- 238000000034 method Methods 0.000 claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 239000012453 solvate Substances 0.000 claims abstract description 42
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 204
- JYGFTBXVXVMTGB-UHFFFAOYSA-N Oxindol Natural products C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 160
- -1 -CH2-pyrazinyl Chemical group 0.000 claims description 135
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 103
- 125000005843 halogen group Chemical group 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 62
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 201000010099 disease Diseases 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 31
- 125000002393 azetidinyl group Chemical group 0.000 claims description 30
- 208000035475 disorder Diseases 0.000 claims description 25
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical group C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 24
- 230000001404 mediated effect Effects 0.000 claims description 22
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001246 bromo group Chemical group Br* 0.000 claims description 20
- 125000003566 oxetanyl group Chemical group 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 206010015037 epilepsy Diseases 0.000 claims description 12
- 201000000980 schizophrenia Diseases 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 206010029216 Nervousness Diseases 0.000 claims description 7
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
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- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- LSMMRJUHLKJNLR-UHFFFAOYSA-N 3-methyl-1,3-benzothiazol-2-one Chemical group C1=CC=C2SC(=O)N(C)C2=C1 LSMMRJUHLKJNLR-UHFFFAOYSA-N 0.000 claims description 5
- MBFOZAKOORJAMK-UHFFFAOYSA-N 4-chloro-3h-1,3-benzothiazol-2-one Chemical group C1=CC=C2SC(O)=NC2=C1Cl MBFOZAKOORJAMK-UHFFFAOYSA-N 0.000 claims description 5
- UAIKQUZQXSTAKX-UHFFFAOYSA-N 7-methyl-1,3-dihydroindol-2-one Chemical group CC1=CC=CC2=C1NC(=O)C2 UAIKQUZQXSTAKX-UHFFFAOYSA-N 0.000 claims description 5
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- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 5
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical group C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims description 4
- UZCYFKUAFQRDKZ-UHFFFAOYSA-N 1-(1H-indazol-7-yl)propan-1-ol Chemical compound N1N=CC2=CC=CC(=C12)C(CC)O UZCYFKUAFQRDKZ-UHFFFAOYSA-N 0.000 claims description 4
- MAIYZXCYLAJOFK-UHFFFAOYSA-N 4-methyl-3h-1,3-benzothiazol-2-one Chemical group CC1=CC=CC2=C1N=C(O)S2 MAIYZXCYLAJOFK-UHFFFAOYSA-N 0.000 claims description 4
- FPDLUAACCNVSQA-UHFFFAOYSA-N 7-chloro-1,3-dihydroindol-2-one Chemical group ClC1=CC=CC2=C1NC(=O)C2 FPDLUAACCNVSQA-UHFFFAOYSA-N 0.000 claims description 4
- VMUIOEOYZHJLEZ-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one Chemical group FC1=CC=CC2=C1NC(=O)C2 VMUIOEOYZHJLEZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000016192 Demyelinating disease Diseases 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- ZRDZFLQIDOBXLG-GORDUTHDSA-N (E)-3-(1H-indazol-7-yl)prop-2-en-1-ol Chemical compound N1N=CC2=CC=CC(=C12)/C=C/CO ZRDZFLQIDOBXLG-GORDUTHDSA-N 0.000 claims description 3
- REHRQXVEAXFIML-UHFFFAOYSA-N 1h-indazole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=NNC2=C1 REHRQXVEAXFIML-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
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- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
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- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 3
- 206010019196 Head injury Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 3
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 3
- 206010028570 Myelopathy Diseases 0.000 claims description 3
- 206010069350 Osmotic demyelination syndrome Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000011235 central nervous system lupus Diseases 0.000 claims description 3
- 208000010353 central nervous system vasculitis Diseases 0.000 claims description 3
- 208000009885 central pontine myelinolysis Diseases 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical group OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 206010061811 demyelinating polyneuropathy Diseases 0.000 claims description 3
- 206010014599 encephalitis Diseases 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000008795 neuromyelitis optica Diseases 0.000 claims description 3
- 201000006292 polyarteritis nodosa Diseases 0.000 claims description 3
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 claims description 3
- 201000000306 sarcoidosis Diseases 0.000 claims description 3
- 208000018198 spasticity Diseases 0.000 claims description 3
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- 239000003053 toxin Substances 0.000 claims description 3
- 231100000765 toxin Toxicity 0.000 claims description 3
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical group C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical group C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical group C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- WCSBQDYJEFXMEX-UHFFFAOYSA-N 3-(1H-indol-5-yl)-2-phenylimidazo[4,5-b]pyridine Chemical compound N1C=CC2=CC(=CC=C12)N1C(=NC=2C1=NC=CC=2)C1=CC=CC=C1 WCSBQDYJEFXMEX-UHFFFAOYSA-N 0.000 claims description 2
- BVXISLUSUVZYIL-UHFFFAOYSA-N 3-(7-phenyl-1H-indazol-5-yl)-2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1(=CC=CC=C1)C=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(F)(F)F BVXISLUSUVZYIL-UHFFFAOYSA-N 0.000 claims description 2
- PGXJMHBTSZQHDD-UHFFFAOYSA-N 4-bromo-3h-1,3-benzoxazol-2-one Chemical group BrC1=CC=CC2=C1NC(=O)O2 PGXJMHBTSZQHDD-UHFFFAOYSA-N 0.000 claims description 2
- DLNMLICVXVLIKO-UHFFFAOYSA-N 4-fluoro-3h-1,3-benzoxazol-2-one Chemical group FC1=CC=CC2=C1NC(=O)O2 DLNMLICVXVLIKO-UHFFFAOYSA-N 0.000 claims description 2
- OJKVOORGQZAZTN-UHFFFAOYSA-N 5-(5-methyl-2-propan-2-ylimidazo[4,5-b]pyridin-3-yl)-1,3-dihydroindol-2-one Chemical compound C(C)(C)C1=NC=2C(=NC(=CC=2)C)N1C=1C=C2CC(NC2=CC=1)=O OJKVOORGQZAZTN-UHFFFAOYSA-N 0.000 claims description 2
- MJFNVTODPOPWPF-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)imidazo[4,5-b]pyridin-3-yl]-1,3-dihydroindol-2-one Chemical compound FC1=CC=C(C=C1)C1=NC=2C(=NC=CC=2)N1C=1C=C2CC(NC2=CC=1)=O MJFNVTODPOPWPF-UHFFFAOYSA-N 0.000 claims description 2
- YUDXLDPOUSOTEF-UHFFFAOYSA-N 6-[2-methyl-6-(trifluoromethyl)pyrrolo[2,3-b]pyridin-1-yl]-3H-1,3-benzothiazol-2-one Chemical compound CC1=CC=2C(=NC(=CC=2)C(F)(F)F)N1C1=CC2=C(NC(S2)=O)C=C1 YUDXLDPOUSOTEF-UHFFFAOYSA-N 0.000 claims description 2
- SCAMUGRWNYLWRU-UHFFFAOYSA-N 6-methyl-1-(7-methyl-1H-indazol-5-yl)pyrrolo[2,3-b]pyridine Chemical compound CC1=CC=C2C(=N1)N(C=C2)C=1C=C2C=NNC2=C(C=1)C SCAMUGRWNYLWRU-UHFFFAOYSA-N 0.000 claims description 2
- NPGZVENVBXJSMQ-UHFFFAOYSA-N 6-methyl-2-phenyl-1-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrrolo[2,3-b]pyridine Chemical compound CC1=CC=C2C(=N1)N(C(=C2)C1=CC=CC=C1)C=1C=C2C(=NC=1)NC=C2 NPGZVENVBXJSMQ-UHFFFAOYSA-N 0.000 claims description 2
- WOUCUAZODBVRKI-UHFFFAOYSA-N 7-chloro-5-(2-propan-2-ylpyrrolo[2,3-b]pyridin-1-yl)-1,3-dihydroindol-2-one Chemical compound ClC=1C=C(C=C2CC(NC=12)=O)N1C(=CC=2C1=NC=CC=2)C(C)C WOUCUAZODBVRKI-UHFFFAOYSA-N 0.000 claims description 2
- LYYJJOICYBLSJE-UHFFFAOYSA-N 7-fluoro-5-(6-methyl-2-propan-2-ylpyrrolo[2,3-b]pyridin-1-yl)-1,3-dihydroindol-2-one Chemical compound FC=1C=C(C=C2CC(NC=12)=O)N1C(=CC=2C1=NC(=CC=2)C)C(C)C LYYJJOICYBLSJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims description 2
- VMGFVGIHYMUYCM-UHFFFAOYSA-N 2-(3-fluorocyclobutyl)-3-(7-methyl-1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC1CC(C1)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=C(C=1)C VMGFVGIHYMUYCM-UHFFFAOYSA-N 0.000 claims 2
- PFVHNBQCQJHKFE-UHFFFAOYSA-N 2-(difluoromethyl)-3-(1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC(C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=CC=1)F PFVHNBQCQJHKFE-UHFFFAOYSA-N 0.000 claims 2
- LYVHKJBOFZCOLZ-UHFFFAOYSA-N 2-(difluoromethyl)-3-(7-methyl-1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC(C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=C(C=1)C)F LYVHKJBOFZCOLZ-UHFFFAOYSA-N 0.000 claims 2
- DRDJQTCBJIIWDG-UHFFFAOYSA-N 2-tert-butyl-3-(1H-indol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C(C)(C)(C)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=CNC2=CC=1 DRDJQTCBJIIWDG-UHFFFAOYSA-N 0.000 claims 2
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- HCCUWWCHPKCGLK-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(3-fluorocyclobutyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C1CC(C1)F HCCUWWCHPKCGLK-UHFFFAOYSA-N 0.000 claims 2
- NXWZCLJJPCMCRQ-UHFFFAOYSA-N 3-(7-methyl-1H-indazol-5-yl)-2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound CC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(F)(F)F NXWZCLJJPCMCRQ-UHFFFAOYSA-N 0.000 claims 2
- IHIMHWKVHKWTJN-UHFFFAOYSA-N 5-(difluoromethyl)-3-(1H-indazol-5-yl)-2-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC(C1=CC=C2C(=N1)N(C(=N2)C(F)(F)F)C=1C=C2C=NNC2=CC=1)F IHIMHWKVHKWTJN-UHFFFAOYSA-N 0.000 claims 2
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- FOFLYVNTHVAXHL-UHFFFAOYSA-N 1-(7-chloro-1H-indazol-5-yl)-2-(3-fluoropropyl)-6-(trifluoromethyl)pyrrolo[2,3-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=CC=2C1=NC(=CC=2)C(F)(F)F)CCCF FOFLYVNTHVAXHL-UHFFFAOYSA-N 0.000 claims 1
- GBWHPNABVPMATA-UHFFFAOYSA-N 1-(7-chloro-1H-indazol-5-yl)-2-methyl-6-(trifluoromethyl)pyrrolo[2,3-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=CC=2C1=NC(=CC=2)C(F)(F)F)C GBWHPNABVPMATA-UHFFFAOYSA-N 0.000 claims 1
- LJTIJHVFRVOLNZ-UHFFFAOYSA-N 1-(7-chloro-1H-indazol-5-yl)-2-methylpyrrolo[2,3-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=CC=2C1=NC=CC=2)C LJTIJHVFRVOLNZ-UHFFFAOYSA-N 0.000 claims 1
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- QGJFIXUJPXFMLA-UHFFFAOYSA-N 1-(7-methyl-1H-indazol-5-yl)-2-propan-2-yl-6-(trifluoromethyl)pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=CC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=C(C=1)C QGJFIXUJPXFMLA-UHFFFAOYSA-N 0.000 claims 1
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- GOJJRTGFRPLVFP-UHFFFAOYSA-N 1-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)pyrrolo[2,3-b]pyridine Chemical compound CC=1C=C(C=C2C=NNC=12)N1C=CC=2C1=NC(=CC=2)C(F)(F)F GOJJRTGFRPLVFP-UHFFFAOYSA-N 0.000 claims 1
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- DFABICRIRMXSCT-UHFFFAOYSA-N 2-cyclopropyl-3-(1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=CC=1 DFABICRIRMXSCT-UHFFFAOYSA-N 0.000 claims 1
- BCUXDMSMHORMDS-UHFFFAOYSA-N 2-cyclopropyl-3-(1H-indazol-5-yl)-5-methoxyimidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)OC)N1C=1C=C2C=NNC2=CC=1 BCUXDMSMHORMDS-UHFFFAOYSA-N 0.000 claims 1
- ZRNALUNDEJPKEX-UHFFFAOYSA-N 2-cyclopropyl-3-(1H-indazol-5-yl)-5-methylimidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)C)N1C=1C=C2C=NNC2=CC=1 ZRNALUNDEJPKEX-UHFFFAOYSA-N 0.000 claims 1
- HZJKBNWEAUZLFQ-UHFFFAOYSA-N 2-cyclopropyl-3-(3-fluoro-2H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C(=NNC2=CC=1)F HZJKBNWEAUZLFQ-UHFFFAOYSA-N 0.000 claims 1
- RDNUUUFBGHUPSX-UHFFFAOYSA-N 2-cyclopropyl-3-(7-methyl-1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C=1C=C2C=NNC2=C(C=1)C RDNUUUFBGHUPSX-UHFFFAOYSA-N 0.000 claims 1
- OEFLRDFUXXWRDB-UHFFFAOYSA-N 2-cyclopropyl-5-(difluoromethyl)-3-(1H-indazol-5-yl)imidazo[4,5-b]pyridine Chemical compound C1(CC1)C1=NC=2C(=NC(=CC=2)C(F)F)N1C=1C=C2C=NNC2=CC=1 OEFLRDFUXXWRDB-UHFFFAOYSA-N 0.000 claims 1
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- RGMHEIVRCSXGHW-UHFFFAOYSA-N 3-(1H-indazol-5-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound N1N=CC2=CC(=CC=C12)N1C=NC=2C1=NC(=CC=2)C(F)(F)F RGMHEIVRCSXGHW-UHFFFAOYSA-N 0.000 claims 1
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- ZMHIBMLSDMSJID-UHFFFAOYSA-N 3-(1H-indazol-5-yl)-N-methyl-5-(trifluoromethyl)imidazo[4,5-b]pyridine-2-carboxamide Chemical compound N1N=CC2=CC(=CC=C12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(=O)NC ZMHIBMLSDMSJID-UHFFFAOYSA-N 0.000 claims 1
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- RQQGZQZHRMIDFI-UHFFFAOYSA-N 3-(3-fluoro-2H-indazol-5-yl)-2-propan-2-yl-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC1=NNC2=CC=C(C=C12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)C RQQGZQZHRMIDFI-UHFFFAOYSA-N 0.000 claims 1
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- NCEVBMGMUYMYAL-UHFFFAOYSA-N 3-(4-methyl-1H-indazol-6-yl)-2-propan-2-yl-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C(C)(C)C1=NC=2C(=NC(=CC=2)C(F)(F)F)N1C1=CC(=C2C=NNC2=C1)C NCEVBMGMUYMYAL-UHFFFAOYSA-N 0.000 claims 1
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- MJTNQSTWFFYACY-UHFFFAOYSA-N 3-(7-bromo-1H-indazol-5-yl)-2-(difluoromethyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound BrC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(F)F MJTNQSTWFFYACY-UHFFFAOYSA-N 0.000 claims 1
- UCVJMWAFARPHJC-UHFFFAOYSA-N 3-(7-bromo-1H-indazol-5-yl)-2-cyclobutyl-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound BrC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C1CCC1 UCVJMWAFARPHJC-UHFFFAOYSA-N 0.000 claims 1
- HPOMIZWRNSJPKR-UHFFFAOYSA-N 3-(7-bromo-1H-indazol-5-yl)-2-propan-2-yl-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound BrC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)C HPOMIZWRNSJPKR-UHFFFAOYSA-N 0.000 claims 1
- JEJXNLJMWCQGHB-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2,5-bis(difluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)F)C(F)F JEJXNLJMWCQGHB-UHFFFAOYSA-N 0.000 claims 1
- VJCLYNBRTPCXJE-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(F)(F)F VJCLYNBRTPCXJE-UHFFFAOYSA-N 0.000 claims 1
- ZKEYKIQPUPDBFE-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2,6-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC=C(C=2)C(F)(F)F)C(F)(F)F ZKEYKIQPUPDBFE-UHFFFAOYSA-N 0.000 claims 1
- SAGMGYIKXBMVIW-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(1,1-difluoroethyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)(F)F SAGMGYIKXBMVIW-UHFFFAOYSA-N 0.000 claims 1
- ICOSESKHYJPVGS-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(1,1-difluoroethyl)-5-methylimidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C)C(C)(F)F ICOSESKHYJPVGS-UHFFFAOYSA-N 0.000 claims 1
- PGLRMXVHQRHDAO-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(1-cyclopropylethyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)C1CC1 PGLRMXVHQRHDAO-UHFFFAOYSA-N 0.000 claims 1
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- CJNGPONAKMOFMJ-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(1-methoxyethyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)OC CJNGPONAKMOFMJ-UHFFFAOYSA-N 0.000 claims 1
- FCWIJKUJVSFILK-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(2,2,2-trifluoroethyl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)CC(F)(F)F FCWIJKUJVSFILK-UHFFFAOYSA-N 0.000 claims 1
- MRXNPLLSAWXTFV-UHFFFAOYSA-N 3-(7-chloro-1H-indazol-5-yl)-2-(2-fluoropropan-2-yl)-5-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound ClC=1C=C(C=C2C=NNC=12)N1C(=NC=2C1=NC(=CC=2)C(F)(F)F)C(C)(C)F MRXNPLLSAWXTFV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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| US201562154313P | 2015-04-29 | 2015-04-29 | |
| US62/154,313 | 2015-04-29 | ||
| PCT/US2016/029801 WO2016176460A1 (en) | 2015-04-29 | 2016-04-28 | Azabenzimidazoles and their use as ampa receptor modulators |
Publications (1)
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| CA2983826A1 true CA2983826A1 (en) | 2016-11-03 |
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| WO2016176457A1 (en) * | 2015-04-29 | 2016-11-03 | Janssen Pharmaceutica Nv | Imidazopyrazines and pyrazolopyrimidines and their use as ampa receptor modulators |
| CN107383004B (zh) * | 2017-07-05 | 2020-04-17 | 浙江大学 | 2-氨基咪唑并吡啶类衍生物及制备和应用 |
| CN111315735B (zh) * | 2017-09-04 | 2024-03-08 | C4医药公司 | 二氢苯并咪唑酮 |
| US11447488B2 (en) | 2017-10-06 | 2022-09-20 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds |
| HUE066335T2 (hu) | 2018-10-05 | 2024-07-28 | Annapurna Bio Inc | Vegyületek és készítmények APJ receptor aktivitáshoz kapcsolódó állapotok kezelésére |
| CN113454080A (zh) * | 2018-10-30 | 2021-09-28 | 修复治疗公司 | 化合物、药物组合物和制备化合物的方法以及其使用方法 |
| EP4003993A4 (en) * | 2019-07-22 | 2023-01-18 | Repare Therapeutics Inc. | SUBSTITUTED 2-MORPHOLINOPYRIDE DERIVATIVES AS ATR KINASE INHIBITORS |
| JP2023554393A (ja) * | 2020-12-16 | 2023-12-27 | アイエフエム デュー インコーポレイテッド | Ｓｔｉｎｇ活性に関連する状態を治療するための化合物および組成物 |
| CN114591338B (zh) * | 2022-03-31 | 2023-05-09 | 苏州欧康维视生物科技有限公司 | 一种Syk和VEGFR2双靶点抑制剂的制备方法及其用途 |
| CN115304599A (zh) * | 2022-09-20 | 2022-11-08 | 浙大宁波理工学院 | 一种3-溴-6-异丙基-1氢-哌咯[2，3-b]并吡啶及其制备方法 |
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| TW251284B (sl) * | 1992-11-02 | 1995-07-11 | Pfizer | |
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| US5565483A (en) | 1995-06-07 | 1996-10-15 | Bristol-Myers Squibb Company | 3-substituted oxindole derivatives as potassium channel modulators |
| UA54403C2 (uk) | 1996-10-01 | 2003-03-17 | Н'Юросерч А/С | Похідні індол-2,3-діон-3-оксиму, фармацевтична композиція, спосіб лікування розладу чи захворювання ссавців, у тому числі людини та спосіб одержання похідних індол-2,3-діон-3-оксиму |
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| WO2000001376A2 (en) * | 1998-07-02 | 2000-01-13 | Eisai Co., Ltd | Pharmaceutical compositions and their uses for treatment of demyelinating disorders |
| CN1356872A (zh) | 1998-12-31 | 2002-07-03 | 苏根公司 | 调节蛋白激酶活性和用于癌症化疗的3－亚杂芳基－2－吲哚满酮化合物 |
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| WO2002014294A2 (en) | 2000-08-11 | 2002-02-21 | Eli Lilly And Company | Heterocyclic sulfonamide derivatives and their use for potentiating glutamate receptor function |
| US6548576B1 (en) | 2001-11-07 | 2003-04-15 | Bourns, Inc. | Epoxy formulation adapted to be used in conjunction with no-lead solder in electronic components |
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| KR101229647B1 (ko) * | 2004-09-03 | 2013-02-05 | 메르크 세로노 에스.에이. | 피리딘 메틸렌 아조리디논 및 포스포이노시타이드 저해제의용도 |
| DE602006019119D1 (de) | 2005-09-30 | 2011-02-03 | Glaxo Group Ltd | Verbindungen mit aktivität am m1-rezeptor und ihre verwendung in der medizin |
| WO2007135529A2 (en) * | 2006-05-23 | 2007-11-29 | Pfizer Products Inc. | Azabenzimidazolyl compounds as mglur2 potentiators |
| JP2010508328A (ja) | 2006-11-03 | 2010-03-18 | グラクソ グループ リミテッド | Ａｍｐａ受容体を強化する化合物および医薬におけるその使用 |
| WO2008113795A1 (en) | 2007-03-20 | 2008-09-25 | Glaxo Group Limited | Compounds which potentiate ampa receptor and uses thereof in medicine |
| GB0711089D0 (en) | 2007-06-08 | 2007-07-18 | Glaxo Group Ltd | Compounds |
| GB0716292D0 (en) | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| WO2009067607A2 (en) | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
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